Re.: 2. Don't worry about the price point atm. He might be right that it is not worth currently for him, but it looks like that a lot of other people value it.

If you continue adding features and continue making the product as a whole better and more valuable for a larger and larger audience.

So eventually he should be happy as well.

That requires obviously, that you mostly add features. i.e. you don't re-invent features or redesign features without adding value (just to make prettier), I have seen a lot of teams/people doing that kind of mistake.